Water → N-{2-[(2-fluoropyridin-3-yl)amino]-4'-methyl-4,5'-bi-1,3-thiazol-2'-yl}acetamide

HRID 1747196Notes

Reaction equation

HRID 1747196 reaction equation
[F:1][C:2]1[C:7]([NH:8][C:9]([NH2:11])=[S:10])=[CH:6][CH:5]=[CH:4][N:3]=1.Br.Br[CH2:14][C:15]([C:17]1[S:21][C:20]([NH:22][C:23](=[O:25])[CH3:24])=[N:19][C:18]=1[CH3:26])=O.O>CCO>[F:1][C:2]1[C:7]([NH:8][C:9]2[S:10][CH:14]=[C:15]([C:17]3[S:21][C:20]([NH:22][C:23](=[O:25])[CH3:24])=[N:19][C:18]=3[CH3:26])[N:11]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 86626613N-(2-fluoropyridin-3-yl)thioureaHCID 87942046N-[5-(bromoacetyl)-4-methyl-1,3-thiazol-2-yl]acetamide, hydrobromide salt2×

Product 1

HCID 11163901N-{2-[(2-fluoropyridin-3-yl)amino]-4'-methyl-4,5'-bi-1,3-thiazol-2'-yl}acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

According to the general procedure 1, N-(2-fluoropyridin-3-yl)thiourea (prepared from 3-amino-2-fluoropyridine (Asymchem), following procedure D) is added to a solution of N-[5-(bromoacetyl)-4-methyl-1,3-thiazol-2-yl]acetamide, hydrobromide salt (Intermediate 1) and TEA (3 eq) in EtOH. The mixture is stirred for 2 h at RT. After addition of water, the desired product is filtrated off and washed with water. N-{2-[(2-fluoropyridin-3-yl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide is isolated as a pale yellow solid (57%).

Workup

  1. filtrationthe desired product is filtrated off
  2. washwashed with water

Sources & evidence

ORD record
ord-59bf13e49d9449a5b9ffea0e8d358896
Source dataset
uspto-grants-2015_10
Patent number
US09150561B2

Reaction notes

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